I had the pleasure of meeting Jacky Wright, Vice President of IT Strategic Services with Microsoft this past weekend at the Women In Business Summit, hosted at the Travelers Claim University in Windsor, CT. The conference’s theme was Lead with Confidence, and Jacky’s message certainly put the audience in the right frame of mind to lead ourselves and our careers with more gumption and choice.

Jacky describes herself as an introvert who has been blessed with a very large and supportive family. Pushing herself out of her comfort zone and being encouraged by those who loved her was how she grew up.

But she also had to overcome that second voice inside the head that plants doubts and fears, that tries to protect you from failure and risk.

Her career trajectory has been fueled by the courageous question:

“What’s the worst thing that could happen?”

Determined to not have any regrets in her life, she has boldly put herself out there, raising her hand for new posts and assignments where the learning curve was steep. She knew that failure is a great teacher and not something to be feared or avoided. She’s been bold in her career, and she has also made decisions that honor her personal priorities. In addition to performing at her demanding job, she is now on the speaker circuit sharing her personal story and pearls of wisdom to others who will follow in her leadership footsteps.

At first, I didn’t know who she was…

I was lucky enough to take a seat at the same table where Jacky was sitting. Not knowing who she was, I just assumed she was one of the participants.  She did not put on any airs. She was a regular person- accessible and humble. But when she took the stage, her beauty and brilliance quickly shone, like the sun rising to greet a new day. I felt grateful for having made the decision to attend this conference  and hear her message.

Please enjoy the following insights and mentoring suggestions from this accomplished business woman, passionate leader, and compassionate mentor – Jacky Wright.

The Stages of Personal Development

Jackie outlined the stages of personal development. She framed the three stages in intriguing thoughts and questions that you might be having.

Stage #1: I can do anything and everything!

In this early career stage, Jacky advised that you seek out networking opportunities. Jacky finds that most early career folks are too quiet, and are hesitant to contribute to the conversation. She encourages you to learn to play to your strengths and to develop your personal brand. Differentiate yourself and use your passions to your advantage. Build a positive professional reputation. Work in such a way that people realize that they can count on you. Let those people know what you are aiming for. Put an “ask” out there.

Stage #2: Where should I invest?

In this mid-career level, it’s time to seek out mentors and sponsors to help advise you and open doors for you. Develop your own board of directors or advisers to give you objective and honest feedback and input. Use this board to validate and challenge your assumptions. Strive for more holistic decision making about your career opportunities. Lastly, align your best opportunities with your goals. Know what you are good at doing and match it with your passions. Move in that direction! Don’t second guess yourself. Just put it out there.

“You have a duty to stretch yourself. Don’t become complacent in your role. Get out of your comfort zone.” – Jacky Wright, Vice President, IT Strategic Services, Microsoft Corporation

Stage #3: What is my legacy?

You’ve been working for several decades. You’ve done a lot and seen a lot, but the game is not over. You may even be ready to re-invent yourself…again. Why not?  Jacky challenges you to be known in your industry. Get a board seat. Expand your leadership via new avenues. Get out of your comfort zone. Get out in the circuit and speak at industry conferences. Share and showcase your thought leadership. Encourage others to rise and contribute. It’s not just about you and what others can do for you. It’s about what you can do for others, and how you will leave the world a better place. How do you want to be remembered?

You don’t have to fit the mold to be successful

During the Q&A, Jacky was asked about perceptions of women in the workplace when it comes to being assertive versus aggressive. She counseled the audience that you need to know the culture that you work in. “Look, I’m a woman. I’m black. I’m a technologist; I don’t fit the mold.” At the end of the day, “it’s about outcome…as long as you don’t leave dead bodies in your wake.”

It’s not just a professional discussion. It’s your life.

Jacky shared a personal story about being afraid to tell her boss that she was pregnant, fearing that she would be eliminated from the consideration set. Her boss found out on his own that she was pregnant after Jacky was in a car accident and he called the hospital to see if she was okay. His call was answered by a nurse in the prenatal care/obstetrics  department. Her boss was surprised that learn that she was 7 months pregnant, and that she didn’t trust him enough to share this personal milestone in her life.

Jacky learned in this experience that”…it’s more than just a career.” It’s your life. “Everyone has to make choices,” she shared. Decide what is most important to you. Share that information with the people that you trust.

Below is the slide that she showed about the factors and decisions that every person needs to consider when building a successful life and career.

Put These Ideas into Action

Identify which stage of personal developments you are currently in. How can you begin to lead with confidence in this stage? What actions do you need to take…with confidence? What connections and relationships do you need to build…with confidence? What limiting beliefs do you need to change in order to allow you to navigate this stage…with confidence? What is the worst thing that could happen to you, should you not succeed the first time? Are you willing to stretch yourself out of your comfort zone… in order to build confidence and create opportunity for yourself and others?

Take that bold step in thought, feeling and action!